JP2002524503A - 二陽イオン分子の抗真菌活性 - Google Patents
二陽イオン分子の抗真菌活性Info
- Publication number
- JP2002524503A JP2002524503A JP2000569796A JP2000569796A JP2002524503A JP 2002524503 A JP2002524503 A JP 2002524503A JP 2000569796 A JP2000569796 A JP 2000569796A JP 2000569796 A JP2000569796 A JP 2000569796A JP 2002524503 A JP2002524503 A JP 2002524503A
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- aminoalkyl
- cycloalkyl
- alkoxyalkyl
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 230000000843 anti-fungal effect Effects 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 238000000034 method Methods 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 13
- 208000031888 Mycoses Diseases 0.000 claims abstract description 13
- 239000003937 drug carrier Substances 0.000 claims abstract description 7
- 230000002538 fungal effect Effects 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 155
- 125000003118 aryl group Chemical group 0.000 claims description 110
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 90
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 90
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 88
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 87
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 82
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 79
- -1 alkoxycycloalkyl Chemical group 0.000 claims description 73
- 125000003282 alkyl amino group Chemical group 0.000 claims description 50
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 22
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 16
- 241000222122 Candida albicans Species 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 241000221204 Cryptococcus neoformans Species 0.000 claims description 5
- 241000427940 Fusarium solani Species 0.000 claims description 5
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 5
- 125000005001 aminoaryl group Chemical group 0.000 claims description 5
- 229940095731 candida albicans Drugs 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
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- 241000233866 Fungi Species 0.000 claims description 3
- 229940091771 aspergillus fumigatus Drugs 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 45
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- 229940121375 antifungal agent Drugs 0.000 abstract description 12
- 238000002560 therapeutic procedure Methods 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 67
- 239000007787 solid Substances 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 238000001819 mass spectrum Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 230000000704 physical effect Effects 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 239000012458 free base Substances 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 13
- 238000009472 formulation Methods 0.000 description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
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- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 11
- 229960004884 fluconazole Drugs 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 10
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- 229910052757 nitrogen Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
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- 239000002054 inoculum Substances 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 8
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- 239000003814 drug Substances 0.000 description 8
- VXAOKODLROCQJS-UHFFFAOYSA-N furan;hydrochloride Chemical compound Cl.C=1C=COC=1 VXAOKODLROCQJS-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
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- 238000003786 synthesis reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- BYDFGYHQOGWROR-UHFFFAOYSA-N 3,4-diamino-n'-cyclopentylbenzenecarboximidamide Chemical compound C1=C(N)C(N)=CC=C1C(=N)NC1CCCC1 BYDFGYHQOGWROR-UHFFFAOYSA-N 0.000 description 5
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- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- PXJJKVNIMAZHCB-UHFFFAOYSA-N 2,5-diformylfuran Chemical compound O=CC1=CC=C(C=O)O1 PXJJKVNIMAZHCB-UHFFFAOYSA-N 0.000 description 4
- UEPHLCIPPLUKCV-UHFFFAOYSA-N 3,4-diamino-n'-propan-2-ylbenzenecarboximidamide Chemical compound CC(C)NC(=N)C1=CC=C(N)C(N)=C1 UEPHLCIPPLUKCV-UHFFFAOYSA-N 0.000 description 4
- QVZGXYWTAPUJRR-UHFFFAOYSA-N 4-(4,5-dihydro-1h-imidazol-2-yl)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1C1=NCCN1 QVZGXYWTAPUJRR-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229960003942 amphotericin b Drugs 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
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- IDSXLJLXYMLSJM-UHFFFAOYSA-N morpholine;propane-1-sulfonic acid Chemical compound C1COCCN1.CCCS(O)(=O)=O IDSXLJLXYMLSJM-UHFFFAOYSA-N 0.000 description 4
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- CWHUCBQOJWVGEF-UHFFFAOYSA-N 1-benzofuran-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C2OC(C=O)=CC2=C1 CWHUCBQOJWVGEF-UHFFFAOYSA-N 0.000 description 3
- QAPAAMJNJUBIMZ-UHFFFAOYSA-N 1-benzofuran;hydrochloride Chemical compound Cl.C1=CC=C2OC=CC2=C1 QAPAAMJNJUBIMZ-UHFFFAOYSA-N 0.000 description 3
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- GTPIEXQPBGBARK-UHFFFAOYSA-N 3,4-diaminobenzenecarboximidamide;hydrate;hydrochloride Chemical compound O.Cl.NC(=N)C1=CC=C(N)C(N)=C1 GTPIEXQPBGBARK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
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- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 3
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- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
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- 229960004130 itraconazole Drugs 0.000 description 1
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- GAIBPHMUUFRRLK-UHFFFAOYSA-N n'-(n'-propan-2-ylcarbamimidoyl)-3-[5-[3-[(e)-n'-(n'-propan-2-ylcarbamimidoyl)carbamimidoyl]phenyl]furan-2-yl]benzenecarboximidamide;dihydrochloride Chemical compound Cl.Cl.CC(C)NC(=N)NC(=N)C1=CC=CC(C=2OC(=CC=2)C=2C=C(C=CC=2)C(=N)NC(=N)NC(C)C)=C1 GAIBPHMUUFRRLK-UHFFFAOYSA-N 0.000 description 1
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- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- PMWXGSWIOOVHEQ-UHFFFAOYSA-N pyridine-2,6-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=N1 PMWXGSWIOOVHEQ-UHFFFAOYSA-N 0.000 description 1
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
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- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 1
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
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- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OTMRXENQDSQACG-UHFFFAOYSA-N thiophene-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C(C=O)S1 OTMRXENQDSQACG-UHFFFAOYSA-N 0.000 description 1
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- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10092898P | 1998-09-17 | 1998-09-17 | |
| US60/100,928 | 1998-09-17 | ||
| PCT/US1999/021383 WO2000015212A2 (en) | 1998-09-17 | 1999-09-15 | Antifungal activity of dicationic molecules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002524503A true JP2002524503A (ja) | 2002-08-06 |
| JP2002524503A5 JP2002524503A5 (enExample) | 2006-10-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000569796A Withdrawn JP2002524503A (ja) | 1998-09-17 | 1999-09-15 | 二陽イオン分子の抗真菌活性 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6326395B1 (enExample) |
| EP (1) | EP1143959B1 (enExample) |
| JP (1) | JP2002524503A (enExample) |
| AT (1) | ATE344028T1 (enExample) |
| AU (2) | AU770656B2 (enExample) |
| CA (1) | CA2344445A1 (enExample) |
| DE (1) | DE69933890T2 (enExample) |
| ES (1) | ES2275362T3 (enExample) |
| WO (1) | WO2000015212A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007513175A (ja) * | 2003-12-05 | 2007-05-24 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | 抗菌剤としてのカチオンで置換されたベンゾフラン |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0016565A (pt) * | 1999-12-20 | 2002-09-17 | Univ North Carolina | Compostos diamidina como ligantes de pequeno sulco de dna |
| US6569853B1 (en) * | 2000-11-06 | 2003-05-27 | Combinatorx, Incorporated | Combinations of chlorpromazine and pentamidine for the treatment of neoplastic disorders |
| CA2455497A1 (en) * | 2001-08-31 | 2003-03-06 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
| AU2003302218A1 (en) | 2002-05-16 | 2004-06-18 | Genelabs Technologies, Inc | Aryl and heteroaryl compounds as antibacterial and antifungal agents |
| CA2504742A1 (en) * | 2002-11-27 | 2004-06-17 | University Of North Carolina At Chapel Hill | Process for synthesis bis-aryl diamidoxime compounds |
| US20050054708A1 (en) * | 2003-07-28 | 2005-03-10 | Nichols Matthew James | Combinations of drugs for the treatment of neoplasms |
| US20050080075A1 (en) * | 2003-08-25 | 2005-04-14 | Nichols M. James | Formulations, conjugates, and combinations of drugs for the treatment of neoplasms |
| US20050100508A1 (en) * | 2003-11-12 | 2005-05-12 | Nichols M. J. | Methods for identifying drug combinations for the treatment of proliferative diseases |
| US20050158320A1 (en) * | 2003-11-12 | 2005-07-21 | Nichols M. J. | Combinations for the treatment of proliferative diseases |
| US7262223B2 (en) * | 2004-01-23 | 2007-08-28 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
| WO2005086754A2 (en) * | 2004-03-08 | 2005-09-22 | Georgia State University Research Foundation, Inc. | Dicationic compounds for activity against trichomonas vaginalis |
| US7994225B2 (en) * | 2004-03-17 | 2011-08-09 | Rempex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors for the treatment of ophthalmic and otic infections |
| EP1732527A2 (en) * | 2004-03-17 | 2006-12-20 | Mpex Pharmaceuticals, Inc. | Use and administration of bacterial efflux pump inhibitors |
| AU2005233632A1 (en) | 2004-04-13 | 2005-10-27 | Icagen, Inc. | Polycyclic pyridines as potassium ion channel modulators |
| DE102004031656A1 (de) * | 2004-06-30 | 2006-01-19 | Merck Patent Gmbh | Tetrahydrochinoline |
| GB0619325D0 (en) * | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| DE102007013854A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Tetrahydrochinoline |
| DE102007013856A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydropyrrolochinoline |
| DE102007013855A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydrochinoline |
| EP2194981B1 (en) * | 2007-10-05 | 2011-11-23 | Université de Mons-Hainaut | Bisbenzimidazoles as antimalarial agents |
| WO2009084544A1 (ja) * | 2007-12-27 | 2009-07-09 | Idemitsu Kosan Co., Ltd. | 含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
| EP3159033B1 (en) | 2008-05-01 | 2019-02-27 | Bayer Intellectual Property GmbH | Catheter balloon drug adherence techniques and methods |
| EP2328910B1 (en) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US11141752B2 (en) | 2012-12-27 | 2021-10-12 | Kateeva, Inc. | Techniques for arrayed printing of a permanent layer with improved speed and accuracy |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2122208A1 (en) | 1971-05-05 | 1972-11-23 | Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | Diamidino-benzimidazole derivs - with fungistatic activity |
| JPS51110531A (en) | 1975-03-26 | 1976-09-30 | Eisai Co Ltd | Amijinokagobutsuno seizoho |
| JPS5922697B2 (ja) | 1976-01-13 | 1984-05-28 | エーザイ株式会社 | ビス−（メタ−アミジノフエノキシ）−化合物 |
| DE2833135A1 (de) | 1978-07-28 | 1980-02-07 | Henkel Kgaa | Verwendung von substituierten oligocarbamidinen als mikrobistatika sowie diese enthaltende antimikrobielle mittel |
| US4397863A (en) | 1980-08-26 | 1983-08-09 | Research Triangle Institute | Inhibition of respiratory syncytial virus-induced cell fusion by amidino compounds |
| US4324794A (en) | 1980-08-26 | 1982-04-13 | Research Triangle Institute | Inhibition of respiratory syncytial virus-induced cell fusion by amidino compounds |
| US4619942A (en) | 1982-04-08 | 1986-10-28 | University Of North Carolina | Inhibition of Respiratory Syncytial virus-induced cell fusion by amidino compounds |
| US4940723A (en) | 1988-10-20 | 1990-07-10 | University Of North Carolina, Chapel Hill | Use of bis-(5-amidino-2-benzimidazolyl) methane (BABIM) to treat arthritis |
| US4963589A (en) | 1988-10-25 | 1990-10-16 | The University Of North Carolina At Chapel Hill | Methods for treating Giardia lamblia |
| US5202320A (en) | 1989-04-06 | 1993-04-13 | Tidwell Richard R | Method for treating leishmaniasis |
| US4933347A (en) | 1988-10-25 | 1990-06-12 | University Of North Carolina At Chapel Hill | Diamidines and bis(imidazolines) for the treatment of and prophylaxis against pneumocystis carinii pneumonia |
| US5206236A (en) | 1989-04-06 | 1993-04-27 | Tidwell Richard R | Method for the treatment of malaria |
| US5428051A (en) | 1992-10-13 | 1995-06-27 | University Of North Carolina | Methods of combating pneumocystis carinii pneumonia and compounds useful therefor |
| US5723288A (en) | 1994-05-06 | 1998-03-03 | The University Of North Carolina At Chapel Hill | Method of fluorescent detection of nucleic acids and cytoskeleton elements using bis-dicationic aryl furans, and kits useful therefor |
| US5602172A (en) | 1994-05-06 | 1997-02-11 | The University Of North Carolina At Chapel Hill | Methods of inhibiting Pneumocystis carinii pneumonia, Giardia lamblia, and Cryptosporidium and compounds useful therefor |
| US5667975A (en) | 1994-05-06 | 1997-09-16 | The University Of North Carolina | Method of fluorescent detection of nucleic acids and cytoskeleton elements using bis-dicationic aryl furans |
| US5521189A (en) | 1994-05-06 | 1996-05-28 | The University Of Nc At Ch | Methods of treating pneumocystis carinii pneumonia |
| US5643935A (en) | 1995-06-07 | 1997-07-01 | The University Of North Carolina At Chapel Hill | Method of combatting infectious diseases using dicationic bis-benzimidazoles |
| US5668166A (en) | 1995-06-07 | 1997-09-16 | Georgia State University Research Foundation, Inc. | Methods of inhibiting pneumocystis carinii pneumonia and compounds useful therefor |
| US5723495A (en) | 1995-11-16 | 1998-03-03 | The University Of North Carolina At Chapel Hill | Benzamidoxime prodrugs as antipneumocystic agents |
-
1999
- 1999-09-15 DE DE69933890T patent/DE69933890T2/de not_active Expired - Fee Related
- 1999-09-15 ES ES99969025T patent/ES2275362T3/es not_active Expired - Lifetime
- 1999-09-15 CA CA002344445A patent/CA2344445A1/en not_active Abandoned
- 1999-09-15 AT AT99969025T patent/ATE344028T1/de not_active IP Right Cessation
- 1999-09-15 WO PCT/US1999/021383 patent/WO2000015212A2/en not_active Ceased
- 1999-09-15 EP EP99969025A patent/EP1143959B1/en not_active Expired - Lifetime
- 1999-09-15 US US09/396,836 patent/US6326395B1/en not_active Expired - Lifetime
- 1999-09-15 AU AU60450/99A patent/AU770656B2/en not_active Ceased
- 1999-09-15 JP JP2000569796A patent/JP2002524503A/ja not_active Withdrawn
-
2004
- 2004-05-26 AU AU2004202311A patent/AU2004202311A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007513175A (ja) * | 2003-12-05 | 2007-05-24 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | 抗菌剤としてのカチオンで置換されたベンゾフラン |
Also Published As
| Publication number | Publication date |
|---|---|
| AU770656B2 (en) | 2004-02-26 |
| WO2000015212A3 (en) | 2001-08-16 |
| ATE344028T1 (de) | 2006-11-15 |
| US6326395B1 (en) | 2001-12-04 |
| DE69933890T2 (de) | 2007-03-15 |
| DE69933890D1 (de) | 2006-12-14 |
| WO2000015212A2 (en) | 2000-03-23 |
| EP1143959B1 (en) | 2006-11-02 |
| EP1143959A2 (en) | 2001-10-17 |
| AU2004202311A1 (en) | 2004-06-24 |
| ES2275362T3 (es) | 2007-06-01 |
| AU6045099A (en) | 2000-04-03 |
| CA2344445A1 (en) | 2000-03-23 |
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